1-(4-chlorophenyl)-1-cyclopentanecarboxylic acid methyl ester | 914106-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-chlorophenyl)-1-cyclopentanecarboxylic acid methyl ester
• 英文别名: methyl 1-(4-chlorophenyl)cyclopentanecarboxylate；methyl 1-(4-chlorophenyl)cyclopentane-1-carboxylate
• CAS: 914106-85-7
• 化学式: C₁₃H₁₅ClO₂
• mdl: MFCD21333130
• 分子量: 238.714
• InChiKey: CRZVZVCCDBEHMG-UHFFFAOYSA-N

物化性质

• 沸点：
  310.7±35.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-1-cyclopentanecarboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.17h， 生成 ethyl 4-(1-(4-chlorophenyl)cyclopentane-1-carboxamido)benzoate
  参考文献：
  名称：

  异羟肟酸酯AR-42的手性衍生物有效抑制I类HDAC酶和癌细胞的增殖。

  摘要：

  在多发性骨髓瘤，白血病和淋巴瘤的临床试验中，AR-42是组蛋白脱乙酰基酶（HDAC）的口服活性抑制剂。它几乎没有氢键供体和受体，但是是手性的2-芳基丁酸酯，可能易于消旋。我们报道了非手性AR-42类似物，其包含通过季碳原子连接的环烷基，对人类I类HDAC的效力提高了40倍（例如，JT86，IC 500.7 nM，HDAC1），对五种人类癌细胞系的细胞毒性增加了25倍，而对正常人类细胞的毒性降低了多达70倍。JT86在促进MM96L黑色素瘤细胞中乙酰化组蛋白H4积累方面比racAR-42强9倍。分子模型和结构-活性之间的关系支持四氢吡喃与HDAC1的结合，而四氢吡喃则是对酶表面水的疏水屏蔽。这种有效的I类HDAC抑制剂可在AR-42活跃的疾病（癌症，寄生虫感染，炎性疾病）中显示出益处。

  DOI：

  10.1021/acs.jmedchem.0c00230
• 作为产物：
  描述：

  对氯苯乙酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 18.17h， 生成 1-(4-chlorophenyl)-1-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  异羟肟酸酯AR-42的手性衍生物有效抑制I类HDAC酶和癌细胞的增殖。

  摘要：

  在多发性骨髓瘤，白血病和淋巴瘤的临床试验中，AR-42是组蛋白脱乙酰基酶（HDAC）的口服活性抑制剂。它几乎没有氢键供体和受体，但是是手性的2-芳基丁酸酯，可能易于消旋。我们报道了非手性AR-42类似物，其包含通过季碳原子连接的环烷基，对人类I类HDAC的效力提高了40倍（例如，JT86，IC 500.7 nM，HDAC1），对五种人类癌细胞系的细胞毒性增加了25倍，而对正常人类细胞的毒性降低了多达70倍。JT86在促进MM96L黑色素瘤细胞中乙酰化组蛋白H4积累方面比racAR-42强9倍。分子模型和结构-活性之间的关系支持四氢吡喃与HDAC1的结合，而四氢吡喃则是对酶表面水的疏水屏蔽。这种有效的I类HDAC抑制剂可在AR-42活跃的疾病（癌症，寄生虫感染，炎性疾病）中显示出益处。

  DOI：

  10.1021/acs.jmedchem.0c00230

文献信息

• THIAZOLIDINONE COMPOUNDS AND USE THEREOF
  申请人：National Health Research Institutes

  公开号：US20170253569A1

  公开（公告）日：2017-09-07

  A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.

  一种含有化合物（I）的药物组合物，用于治疗与阿片受体相关的疾病。还公开了一种使用这种化合物治疗阿片受体相关疾病的方法。进一步公开了两组式（I）的噻唑烷酮化合物：（i）每种化合物的对映体过量大于90%；（ii）每种化合物被氘取代。
• Gamma lactams as prostaglandin agonists and use thereof
  申请人：Araldi Luca Gian

  公开号：US20050288357A1

  公开（公告）日：2005-12-29

  1,2-substituted 5-pyrrolidinone compounds are provided, and methods of treatment and pharmaceutical composition that utilize or comprise one or more such compounds. Compounds of the invention are useful for a variety of therapies, including treating or preventing preterm labor, dysmenorrhea, asthma, hypertension, infertility or fertility disorder, undesired blood clotting, preeclampsia or eclampsia, an eosinophil disorder, sexual dysfunction, osteporosis and other destructive bone disease or disorder, renal dysfunction, an immune deficiency disorder, dry eye, ichthyosis, elevated intraocular pressure, sleep disorder, or gastric ulcer, inflammatory disorders and other diseases and disorders associated with the prostaglandin family of compounds.

  本发明提供了1,2-取代的5-吡咯烷酮化合物，并提供了利用或包含一个或多个此类化合物的治疗方法和制药组合物。本发明的化合物可用于各种治疗方案，包括治疗或预防早产、痛经、哮喘、高血压、不孕或生育障碍、不良血液凝固、先兆子痫或子痫、嗜酸性粒细胞异常、性功能障碍、骨质疏松和其他骨骼疾病或障碍、肾功能障碍、免疫缺陷性疾病、干眼症、鱼鳞病、眼内压升高、睡眠障碍或胃溃疡、炎症性疾病和其他与前列腺素类化合物有关的疾病和障碍。
• Thiazolidinone compounds and use thereof
  申请人：National Health Research Institutes

  公开号：US10544113B2

  公开（公告）日：2020-01-28

  A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.

  一种含有用于治疗阿片受体相关疾病的式 (I) 化合物的药物组合物。还公开了一种使用此类化合物治疗阿片受体相关疾病的方法。进一步公开了两组式(I)的噻唑烷酮化合物：(i)对映体过量大于 90%的化合物和(ii)各自被氘取代的化合物。
• Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes
  作者：Louis Crane、Maria Anastassiadou、Salomé El Hage、Jean Luc Stigliani、Geneviève Baziard-Mouysset、Marc Payard、Jean Michel Leger、Jean-Guy Bizot-Espiard、Alain Ktorza、Daniel-Henri Caignard、Pierre Renard

  DOI：10.1016/j.bmc.2006.07.026

  日期：2006.11

  Imidazoline derivatives have been reported to show anti hyperglycemic activity in vivo. In the present study, we first showed that there was no correlation between the in vivo antidiabetic activity and the in vitro affinities for the I-1/I-2 binding sites for several substituted daryl imidazolines. Among these compounds, 2-(alpha-cyclohexyl-benzyl)-4,5-dihydro-1H-imidazole 2 exhibited potent antihyperglycemic properties. It was then chosen as lead compound. Thirty-six new derivatives were synthesized by replacing the cyclohexyl/benzyl group by various cyclic systems or the imidazoline ring by isosteric heterocycles. These compounds were evaluated in vivo for their antihyperglycemic activity using an oral glucose tolerance test (OGTT) in a rat model of type-2 diabetes obtained by giving a single intravenous (iv) injection of a low dose of streptozotocin to rats (STZ rats) and in normal rats. Nine compounds with an imidazoline moiety, possibly substituted by a methyl group, had a potent effect on the glucose tolerance in normal or STZ-diabetic rats, after an oral (po) administration of the test compound at a dose of 30 or 10 mg kg(-1) without any hypoglycemia. Replacement of the imidazoline ring by isosteric heterocycles resulted in a total loss of activity. (c) 2006 Elsevier Ltd. All rights reserved.
• [EN] GAMMA LACTAMS AS PROSTAGLANDIN AGONISTS AND USE THEREOF<br/>[FR] GAMMA LACTAMES UTILISES EN TANT QU'AGONISTES DE LA PROSTAGLANDINE ET LEUR UTILISATION
  申请人：——

  公开号：WO2003103604A3

  公开（公告）日：2004-02-12